In 1984, while still a medical student, Pinsky started appearing in "Ask a Surgeon", a segment of a Sunday night KROQ-FM show hosted by Jim "Poorman" Trenton and "Swedish" Egil Aalvik.[12] "Ask the Surgeon" soon combined with "Loveline", another Sunday night segment, into a show of its own, co-hosted by Trenton and Pinsky. Loveline went national in 1995, and the television version launched on MTV the following year, hosted by Pinsky and Adam Carolla. The exposure on both radio and television made Pinsky the "Gen-X answer to Dr. Ruth Westheimer, with an AIDS-era, pro-safe-sex message."[11] The MTV show ran for four years, while the radio show continued until April 2016 with cohost Mike Catherwood.

On November 27, 2007, Pinsky began Dr. Drew Live, another nationally syndicated talk radio show where he focused on a wider range of health issues. It originated from KGIL in Los Angeles, originally airing weekdays from 11:00 am to 1:00 pm PT[13] The show was canceled in December 2008.

On January 5, 2015, Pinsky launched a new weekday program, "Dr. Drew Midday Live with Mike Catherwood," on KABC in Los Angeles.[14]

On April 21, 2016, Pinsky announced Loveline would wrap up on April 28, 2016. Adam Carolla re-joined him as co-host for the final show. [15]

Pinsky's first television appearance was as a contestant on Wheel of Fortune in 1984, though he did not win. He also served as "health and human relations expert" on the first season of the U.S. TV series Big Brother in 2000.

In 2008, Pinsky starred in Celebrity Rehab with Dr. Drew, a reality television show which involves celebrities in a drug rehabilitation facility. The show was filmed at Pasadena Recovery Center, with Pinsky serving as the resident medical expert. The series premiered January 10, 2008 on VH-1, and has been renewed for multiple seasons. A follow-up show to Celebrity Rehab with many of the same celebrities was Sober House, which began its first season in January 2009, and included celebrities from the first two seasons of Celebrity Rehab continuing their recovery in a sober living facility.[16] In November 2009, Pinsky starred in a spinoff of Celebrity Rehab, Sex Rehab with Dr.Drew, which depicted celebrities being treated for sexual addiction over the course of three weeks at the Pasadena Recovery Center.

Pinsky makes guest appearances on a variety of news programs where he usually gives his observations on the relationship between controlled substances and high-profile individuals. He has frequently given his views on the deaths of people such as Anna Nicole Smith, Heath Ledger and Michael Jackson, arguing that their fates should set examples of the seriousness of misusing drugs.[17]

In early 2011, Pinsky began hosting his own show, Dr. Drew On Call on HLN that focuses on news involving health and addiction topics.[24] On August 26, 2016, HLN and Pinsky announced that the show's last episode would be September 22 of that year.[25]

In 1999, Pinsky co-founded an Internet-based community and advice site for teenagers called DrDrew.com with Curtis Giesen. Among their early backers was Garage.com.[26] DrDrew.com soon ran out of funding, and the company was sold to Sherwood Partners Inc., a corporate restructuring firm, which sold the remnants to DrKoop.com in November 2000.[27] Pinsky re-acquired the site circa 2013 and began using for general information about his books, radio and TV shows, as well as hosting his independent podcast, The Dr. Drew Podcast.[28] In September 2012, Pinsky announced on the The Adam Carolla Show that he will be doing a podcast on the Carolla Digital network.[29]

In addition to his media appearances, Pinsky speaks at college campuses and other public venues.[30][31] When Adam Carolla and Pinsky were teamed as hosts of Loveline, Carolla and Pinsky spoke at colleges.[32][33][34]

Pinsky married on July 21, 1991, and he and his wife, Susan Sailer, had triplets Douglas, Jordan, and Paulina in November 1992.[47][48][49]

Pinsky lives in Pasadena, California. Interested in fitness since his early teens, he goes running[50] and does weight training regularly.[51] In addition to his hobby of traveling,[12] he also enjoys singing opera, as his mother was a professional singer. Pinsky stated on the June 24, 2009 episode of Loveline that at one point, he was torn between practicing medicine and becoming a professional opera singer.[52] Pinsky stated that he auditioned for a celebrity singing show, but that the show passed on his appearance when he made it clear to producers that he could not sing pop songs, but did perform an aria on Turn Ben Stein On.[53][54][55]

Pinsky is a nonobservant Jew; he admits to abandoning most Jewish practices but claims to retain a continued desire to learn about the religion. He explains that religious as well as philosophical studies affect his medical practice and his speeches, and that his background places "an indirect coloring on every answer."[57]

In September 2013, Pinsky revealed that he had recovered from prostate cancer surgery performed earlier that June and July, after which Pinsky did not require chemotherapy or radiation.[58]

In an interview on Kevin and Bean, Pinsky has stated he will speak to any media outlet including TMZ and The National Enquirer, but will not speak to the Los Angeles Times, explaining "They distort, and they mislead, and they take things out of context. I really am stunned at how shoddy their journalism is, so I stopped talking to them."[59]

Politically, Pinsky has increasingly spoken of the 'tyranny' of governmental overreach and the need for a “Liberty Party.”[60]

Pinsky, Dr. Drew; with Robert Meyers; William White (July 2004). When Painkillers Become Dangerous: What Everyone Needs to Know about OxyContin and Other Prescription Drugs. New York: Hazelden Publishing & Educational Services. ISBN1-59285-107-X.